Is It Ever OK to Date a Friend’s Ex You’re Chatting to on an Online Dating Site?

If you are thinking of going on a date with your friend’s Ex that you’ve been chatting with on an online dating site, you have to decide if it is really OK.

Not only do you have to deal with how your friend feels about it, but you should also make sure that the Ex in question knows you are still close to their Ex too.

How does it happen?

Believe it or not, it is easier than you think to run into a friend’s Ex on an online dating site.

Most of the sites are based on geography so there are only a limited number of people available in your area and age range, so you are bound to see each other in your search results.

What happens next is that the two of you already have some knowledge of each other, and that can lead to conversations starting.

Before you know it, you and your friend’s Ex are chatting away on an online dating site.

Do you need to ask permission?

Here is when it gets tricky.

The real question about is it ever OK to date a friend’s Ex you’re chatting to on an online dating site involves whether or not there is an issue of permission.

Why would you need “permission” as an adult to talk to someone?

Because your friendship should have priority over someone new – it wouldn’t matter who it was.

There are some general rules of thumb you can follow about making sure that you have “permission” without doing something as stupid as actually asking for it.

  • Let your friend know that you have run into their Ex on the dating site.
  • Let your friend know that you have exchanged some messages with them.
  • Only ask them if they are OK with that if you are prepared to stop messaging the Ex if your friend isn’t good with the idea.

That last is very important.

Don’t open a door for your friend to draw a boundary if you aren’t prepared to respect it by either ending the friendship or stopping talking to the Ex.

Either way you should always at least mention that you have met them online and have exchanged messages – if, that is, the Ex is still considered an Ex.

When is an Ex no longer an Ex?

You know your friends best, and you will know if the ‘love of their life who ruined them’ that they dated when they were in 9th grade is still a big deal, or whether they aren’t.

Just because your friend dated, or even married and divorced someone, doesn’t mean that you have to cling to the relationship or its demise.

  • She isn’t an Ex if they dated for less than 6 months.
  • She is definitely an Ex if they were married.
  • She isn’t an Ex if they were in a serious relationship that ended 5 years prior from your meeting.

On the last, this can be difficult as it can take some people an awful long time to move on.

After 5 years though, it isn’t about the relationship – it is your friend’s issue and not yours.

What to do if that chat turns into a date?

Trying to decide if it is ever OK to date a friend’s Ex you are chatting with on an online dating site is tricky.

It shouldn’t be a reason not to chat with the Ex, but when you get to the point that the chat is going to move to a real time date, and then it’s time to think all of this through.